Product of the anthraquinone series and process of making same.



UNITED. STATES mm OFFICE.

FRITZ ULLMANN, or cHAnLorrnNBUnc, GERMANY, ASSIGNOR To Ac'rIEN GESELL- scnu'r Fun ANIL'IN FABRIKATION, or BERLIN, GERMANY.

PRODUCT F 'ISHE ANTHRAQUINONE SERIES AND PROCESS OFMAKING SAME.

1,001,325. No Drawing.

Patented Aug. 22, 1911.

To all whom 'it may concern: Be it known that I, FRITZ ULLMANLN, a subject of the King of Bavaria, residing at Charlottenburg, near Berlin, Germany, my post-ofiice'address being Schillerstrasse 15/16, Charlottenburg', near Berlin, Germany,lhave invented certain new and useful Improvements in New Products of the An ,thraquinone Series andProcesses of Making the Same, of which the following is a speci fication.

My present invention relates to new products of the anthraquinone series and the process for the manufacture of the same consists in acting upon an anthraquinonealpha-carboxylic'acid, that is .to say upon I or a derivative of this acid, with a hydrazin, such as, for instance .phenylhydrazin or bromphenylhydrazin, etc. The reaction which is the base of my invention appears to take place according to the following equation coon +mn. NH. 0. V i N-om,

I 0 i I 00 starting for instance from antraquinone" allpha-carboxylic acid and phenylhydrazin. T ese new bodies may serve as intermediate roductsffor the manufacture of dyesor as of reaction may be altered within widelimr to'be obtained.

. tained bf'imcting solves, then after some time the product of acid-the product dissolves to an orange so lution having a weak green fluorescence.

'It is obvious that my present invention is not limited to the foregoing example or to the details given therein; Thus, for instance, instead of phenylhydraz'in I can employ phen'ylhydrazin-sulfonic acid or bromphenylhydrazin' or hydrazin' itself, etc. Furthermore for the anthraquinone-alphacarbonylic acid used in the above example I can substitute for instance lA-chloi'a'nthraquinone carboxylic acid. or Lfi-nitro- 7.5,

- anthraquinone carboxylic-acid or the chloridof anthraquinone-alpha-carboxylic acid, etc.-

In using such other parent materials for'my,

new process, ofcourse, the special conditions its, without departing from the scope ofmy invention, according to the] nature of the parent materials as well as of the products Having now describedliny'invention-and" the mannerlin which it ma'yperformed What I claim, is,"

1. As new articles of manutactu'r'e the new products of the anthraquinone series, L y

;having. the general formula:

. 1(. to L .95

in'which formula It means a non-metallic substituent', which new products'ma'y be obwitlra hydrazin-upon .a'n anthraquinon'e-a ph-a-carbo lic acid, these Y new products bem in the shape when pulverized, yellowlsh to yel ow powders, very difiicult y soluble in alcohol and ether and soluble in lp' 'vridin.to a yellow solution, whereas they issolvein concentrated sul- {uric acid to a yellow to an orange solution v havin a weak fluorescence.

new articles of manufacture the new roducts of the anthraquinone series, havmg the general formula:

upon an anthraquinone-alpha-carboxylic acid, these new products being in the dry shape when pulverized, yellowish to yellow powders,- very diflicultly soluble in alcohol and ether and soluble in pyridin to-a yellow solution, whereas they dissolve in concentrated sulfuric acid to a yellow to an orange solution having a weakfluorescence.

3. As a new article of manufacture thev new' product of the anthraquinone series, having the formula:

k/ which new product may he obtained by acting with phenylhydrazinupon an anthraqu1nonealphacarboxylic acid, this new product being in the dry shape when pulverized, a yellowish to yellow powder, very diificultly soluble in alcohol and ether and soluble in pyridin to a yellow solution, whereas it dissolves in concentrated sulfuric acid to a yellow to an orange solution having a weak fluorescence.

In testimony whereof I have hereunto set my hand in presence of two subscribing witnesses.

FRITZ ULLMANN.

, WVitnesses:

HENRY HASPER, WOLDEMAR HAUPT. 

